2-METHYL-4-HYDROXYMETHYLPYRIDINE

In a variation of the above procedure, a solution of 2-chloro-6-methylpyridine-4-carboxylic, palladium (0.20 g, 10 mol percent on carbon), ethyl acetate (45 mL), and triethylamine (2.8 mL, 20 mmol). The reaction mixture was placed under hydrogen at 1 atm for 21 hours. Additional Pearlman's catalyst (0.2 g) was added and the reaction was stirred under hydrogen for an additional 5 hours to effect dechlorination. The mixture was filtered through a pad of celite and concentrated. Purification by column chromatography (5:95 methanol:dichloromethane) gave (2-methyl-pyridin-4-yl)-methanol (1.48 g, 88percent). The (2-methyl-pyridin-4-yl)-methanol was used to prepare 2-amino-3-(2-methyl-pyridin-4-yl)-propionitrile, from which 1-methyl-1H-indole-2-carboxylic acid ((1S, 2R)-2-{[cyano-(2-methyl-pyridin-4-ylmethyl)-methyl]-carbamoyl}-cyclohexyl)-amide was obtained (186 mg, 62percent) in the manner described above. MS: 444 (M+H).(2-Methyl-pyridin-4-yl)-methanol:; Acetic acid 2-methyl-pyridin-4-ylmethyl ester (5.1 g, 31 mmol) was stirred with ammonium hydroxide (10 ml) in methanol (25 ml) at room temperature. After 24 hr., the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA) to afford 3.56 g (94percent) of (2-methyl-pyridin-4-yl)-methanol as a pale yellow solid. m.p. 58-59° C. A.

Molecular Weight:123.15
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:123.068413911
Monoisotopic Mass:123.068413911
Topological Polar Surface Area:33.1
Heavy Atom Count:9
Complexity:85
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes